In the skillet over medium heat, cook the bacon pieces until slightly crispy and the fat is rendered. Remove the bacon and drain on a paper towel. Reduce the heat to medium low.
In the small bowl, stir the balsamic vinegar and sugar together until the sugar dissolves. Add the mixture to the skillet and stir until it warms. Add the roasted garlic cloves and cook at a simmer for 3 to 4 minutes. Season with the black pepper.
Arrange the chard leaves among 4 plates, add some radicchio and divide the asparagus spears among the plates. Top each plate with sun-dried tomato slices and roasted garlic cloves, then drizzle the bacon vinaigrette on top. Serve immediately.